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Vacation Rentals in Osage County

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Top Vacation Rentals in Osage County

Scenic Lakeside Chateau with Heated Pool, Hot Tub & Outdoor Kitchen-TV-Fireplace

10.0 out of 10, Exceptional, (220)
"Such a great place to connect with family or friends. "
Scenic Lakeside Chateau with Heated Pool, Hot Tub & Outdoor Kitchen-TV-Fireplace

Entire Cabin in Linn, MO with all the extras

10.0 out of 10, Exceptional, (8)
"We had a lovely stay. The cabin was in pristine shape and had everything we needed to enjoy our stay. Roxie was accommodating and responsive. We would definitely stay again. "
The price is ¥29,402
¥33,224 total
includes taxes & fees
Oct 5 - Oct 6
Entire Cabin in Linn, MO with all the extras

Cozy house nestled in the country

10.0 out of 10, Exceptional, (18)
"Very cozy, plenty of space, well maintained. We had a great time!"
Cozy house nestled in the country

The Mercantile on the Katy Trail

4.5 star property
9.8 out of 10, Exceptional, (23)
"Nice quiet area with open concept space inside."
The price is ¥30,210
¥32,317 total
includes taxes & fees
Oct 6 - Oct 7
The Mercantile on the Katy Trail

Country Container Tiny House. Experience peace by the water & native wildlife!

2.0 star property
10.0 out of 10, Exceptional, (3)
"Fun unique place to stay"
The price is ¥13,966
¥19,111 total
includes taxes & fees
Oct 5 - Oct 6
Country Container Tiny House. Experience peace by the water & native wildlife!

Suite on Schiller

9.8 out of 10, Exceptional, (110)
"Great place to stay and location was perfect."
Suite on Schiller

Cozy Cabin in the woods near charming Hermann

Cozy Cabin in the woods near charming Hermann

Ash Creek Suite - In Downtown Historic Hermann

9.4 out of 10, Exceptional, (49)
"Great location in a lovely town."
The price is ¥29,402
¥51,076 total
includes taxes & fees
Oct 5 - Oct 6
Ash Creek Suite - In Downtown Historic Hermann

Private Logcabin All To Yourself With Lake View

9.8 out of 10, Exceptional, (214)
"Very cool rustic cabin with a neat history."
Private Logcabin All To Yourself With Lake View

Glamping with gorgeous sunset views, trolley to all wineries

9.4 out of 10, Exceptional, (6)
"It was a wonderful stay for 5 of us girls going to Herman for a day at the Winery. This location was perfect, just 7 minutes up the road from Downtown Herman. The trolley picked us up with no issue. Very quiet location, perfect for a quick getaway!"
The price is ¥22,052
¥33,519 total
includes taxes & fees
Oct 7 - Oct 8
Glamping with gorgeous sunset views, trolley to all wineries

Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO

10.0 out of 10, Exceptional, (147)
"We stay here each year for a bike race weekend. We really enjoy the space and the location!!"
Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

9.6 out of 10, Exceptional, (99)
"Great stay . Perfect for 3 couples. House was exactly as described with a great location. Would 100% stay here again! "
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

Cozy Riverview Cottage. 5 minute walk to downtown

10.0 out of 10, Exceptional, (33)
"We had a great stay at Autzie’s and was the perfect setting for our 20th wedding anniversary getaway. Thanks"
The price is ¥26,462
¥38,967 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Riverview Cottage. 5 minute walk to downtown

The Van Gogh Suites is one of our four rooms.

9.6 out of 10, Exceptional, (35)
"This was our second time to say at the Artist Suites. We enjoy staying here because each suite is unique and we like the downtown location. Next time we visit Hermann we will once again stay here "
The price is ¥16,029
¥28,181 total
includes taxes & fees
Nov 2 - Nov 3
The Van Gogh Suites is one of our four rooms.

Unique traincar stay at the Katy Caboose!

9.4 out of 10, Exceptional, (6)
"My wife and I stayed for two nights to celebrate our 19yr anniversary. We got a bike ride in on the Katy and checked out local watering holes. The Katy Caboose was cute. We enjoyed the deck on a beautiful starry night."
The price is ¥14,392
¥25,935 total
includes taxes & fees
Oct 14 - Oct 15
Unique traincar stay at the Katy Caboose!

Wine Alley East suite

9.4 out of 10, Exceptional, (72)
"Great place"
The price is ¥21,316
¥31,129 total
includes taxes & fees
Oct 12 - Oct 13
Wine Alley East suite

The Carriage House at Parker's Place

10.0 out of 10, Exceptional, (40)
"Carefully re-habbed. Tastefully decorated. "
The price is ¥26,273
¥38,490 total
includes taxes & fees
Oct 5 - Oct 6
The Carriage House at Parker's Place

Treehouse - Sunrise

2.0 star property
10.0 out of 10, Exceptional, (13)
"5 star stay!"
Treehouse - Sunrise

New - custom-built Treehouse - Twilight

10.0 out of 10, Exceptional, (3)
"The twilight cabin was so clean and cozy. We enjoyed our stay. "
New - custom-built Treehouse - Twilight

The Pollock Suite is one of our four rooms.

9.8 out of 10, Exceptional, (62)
"We had a really nice stay and would definitely book again."
The price is ¥16,029
¥28,181 total
includes taxes & fees
Nov 2 - Nov 3
The Pollock Suite is one of our four rooms.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Osage County Hotel Reviews

Find out more about Osage County

Find out more about Osage County

Vacation Apartments in Osage County

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